I'm guessing the dropbox one and the character one are both cases of swapping terms in math like say calculating your age by subtracting the current year from the year you were born instead of subtracting the year you were born from the current year. It's a common mistake. The dropbox one makes perfect sense in that context as default Basic account is 4GB, plus the 3 GB bonus is 7GB. 7GB-48GB = -41GB. I suspect their calculation was originally geared towards people buying space and was basic + bought = new_total and somewhere along the lines someone thought "Oh, let's handle accounts expiring by just shoving a negative value into the bought variable. In which case they should probably just make their equation abs(basic + change) = new_total and call it a day.

explorer.exe message is not WTF. Just not really helpful error boy. (WaitForSingleObject can have time limit, after which it errors out)
No WTF/Error'd...
(https://msdn.microsoft.com/en-us/library/windows/desktop/ms687032.aspx)

Worms 2 had a progress bar that animated while it was generating the level. However the animation was on a timer and unrelated in any way to the actual progress the game was making in the generation of the level. Occasionally you would even see it wrap around and start over.

Yeah, but if they just mean his limit will be 41 GB lower than it is now, the 1 GB of space he's using right now shouldn't be a problem after it changes. So it makes no sense to tell him that he's at risk of being above his new limit.